The Player’s Box – Episode 13 Summary

Episode Title: What Would You Do & Winners of the Week
Release Date: November 18, 2025
Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk

Episode Overview

This episode dives into the behind-the-scenes realities of life on the tennis tour with candid, funny stories from the four hosts. They kick off with their classic “Unforced Error or Winner of the Week” segment, delve into a tennis-themed “What Would You Do?” hypothetical game, discuss the tricky business of coaching changes, and field fan questions about everything from racquet dampeners to favorite clothing brands. Caffeine, chaos, and laughter abound.

Highlights & Key Discussion Points

1. Unforced Error or Winner of the Week

Segment starts: 00:27

Each host shares a recent mishap (“unforced error”) or positive highlight (“winner of the week”) from their personal lives.

• Madison Keys:
  • Winner: The rare Florida winter—enjoyed the cold weather and pulling out winter clothes.

    “I got to pull out all of my warm clothes. Jenny wanted to die, but I thought it was the greatest time ever.” [00:50]

• Jessica Pegula:
  • Winner: She's on vacation in the Bahamas on a boat, happy and thriving.

    “I am on a boat in the Bahamas and I’m thriving.” [01:21]

• Jennifer Brady:
  • Unforced Error: Accidentally walked in on a man in the airplane lavatory after misreading the lock.

    “I went to open the door because it said unlocked, and it was. Supposed to be locked because there was just a man, you know, sitting on the toilet…” [01:46]

• Desirae Krawczyk:
  • Unforced Error: Her dog Pluto was neutered, had a messy accident in the middle of the night with the cone on, resulting in a “farting noise” and diarrhea on the floor.

    “And it’s just like him looking at me like this, like, puppy dog eyes and just diary on the floor.” [03:21]

Memorable Group Banter:

• Generous teasing about who “wins” the week; consensus is Jess gets it for being on a boat.
• “That’s an unforced error for that guy in the plane bathroom. That’s so bad. Also, poor Pluto.” – Pegula [04:07]

2. Life Updates & Bachelorette Plans

Segment starts: 05:00

• Jenny and Des are recording together in LA ahead of a friend’s “chill” bachelorette—pajamas, s'mores, pizza, no alcohol.

  “It’s going to be like pajamas, board games, s’mores... pizza. It’s going to be chill.” – Desirae [05:52]

• Technical difficulties abound, especially with Jess lagging from the Bahamas.

3. What Would You Do? – Tennis Edition

Segment starts: 06:25

A new segment with chaotic and funny tennis hypotheticals.

• You accidentally celebrate a point that wasn’t yours—how do you play it off?

  • “You kind of just turn it into a ‘Come on, next point, next point’ instead of ‘Come on, I won that point!’” – Brady [07:44]
  • Real-life examples: third-set tiebreakers confusion, early celebration mishaps.

• How do you mentally reset when losing to someone you think you’re better than?

  • “You cave, lose your mind.” – Keys [10:10]
  • “You just fully crash out.” – Pegula [10:15]
  • “You tell yourself, I need to touch grass.” – Brady [10:25]

• Opponent calls a physio timeout right before you serve. What do you do?

  • “There are so many girls that do it on tour… I have a few that come to mind.” – Krawczyk sassing [11:10]
  • Jess reminds Desirae of a specific time she called for a leg re-tape before a 10-point tiebreaker:

    “I was against you and I was like, seriously, Des, wait against me to get your leg re-taped…” [11:45]

• You shank a ball and hit a child in the stands. How do you recover?

  • “I think you give the two, like, double hands, like, ‘I’m sorry,’ and hope he or she is okay…” – Brady [13:01]
  • Stories about shanking balls, almost hitting partners, ball kids, and even a player’s mom.
  • “Have you ever shanked a ball where, like, it hits… the top and hits the outside?” – Pegula [13:33]

• Rain delay protocol?

  • “Definitely a nap, 100%.” – Krawczyk [16:18]
  • “I don’t nap, so probably eat. Round two, maybe three. Steak—no, not before a match—chicken and rice…” – Brady [16:22]
  • Overanalyzing how close the hotel is and rain-delay logistics.

• When kids hold umbrellas for you on court, is it awkward?

  • “I feel so bad. I’m like, no, I’ll hold it. Come sit down so that we’re both under the umbrella and not just getting poured on.” – Keys [19:28]

4. Coaching Changes: Firing, Hiring, and Tour Gossip

Segment starts: 19:59

• The annual shuffle: November is when many players change coaches, doubles partners, or teams.

• Processes:

  • “Firing: You just don’t want to work with them anymore… a lot of players do trials, just try coaches for a couple months.” – Pegula [20:23]
  • “I’ve probably changed coaches the most of the four of us. Sometimes it’s mutual, sometimes it’s because I’ve had a few cuckoo coaches.” – Keys [22:38]
  • Public nature of coach changes can amplify drama online.

• Poaching & Behind-the-scenes Shadiness:

  • “Other coaches are poaching players… and then the next week, they’re at a tournament with a different player. That’s, like, really shady.” – Brady [25:33]
  • “There’s definitely players that… start looking for replacements before they’ve finished with their coach... I’ve had coaches be like, ‘Are you looking for someone?’ and you’re like, ‘Aren’t you with someone else?’” – Keys [26:31]

• Memorable moments:

  • “I had a coach last two weeks… I found 13 alcoholic drinks charged to my room and added to the expense… I lost it, but I was so happy.” – Krawczyk [27:52]
  • Pegula: “Maddie’s like, setting the bridge on fire.” – [30:14]
  • Keys: “Yeah, like, I don’t talk to coaches that coached you all because you’re like, ‘this one time they did this,’ and I’m like, dead.” [30:25]

• Surprising coaching pairings:

  • Discussion of Andy Murray coaching Novak Djokovic:

    “I don’t think we’ve ever seen them, like, rivals… in the same era, work together.” – Keys [31:16] “If you’re Andy, you probably want to know literally everything… what he does for his body, how he’s able to do what he does…” – Brady [33:30]

• Marat Safin & Dinara Safina:

  • Fan-girling over Safin joining the tour as a coach; stories about his abs, cigarettes, outgoing personality, memories from childhood crushes.
  • “He truly just doesn’t care. But he’s so funny and engaging…” – Pegula [35:11]

5. Fan Q&A

Segment starts: 36:30

Fan questions spark more personal anecdotes and rapid-fire debates:

• Dampeners: Do you use them? Do they make a difference?

  • “I do not. I do think they make a big difference, but I always like the way it sounds when I don’t use them.” – Pegula [36:55]
  • “I’ve always used one because I hated the pinging sound… But sometimes I take them out and I’m like, ‘See, now all of a sudden I’m hitting the ball exactly where I want it.’” – Keys [37:04]
  • “As I got older, I saw Saffin wasn’t using one… since then, I haven’t gone back. I do enjoy the little ping.” – Brady [38:02]

• USTA Flex League singles advice:

  • “Don’t hit in the alleys.” – Krawczyk [40:06]
  • “Big targets. Start aiming for the middle of the court…” – Brady [40:10]
  • “Incorporate some of your doubles stuff, come to the net if that’s your strength.” – Krawczyk [40:39]

• Have you ever served without bouncing the ball?

  • “No.” (All around) [41:30]
  • “I’ve tested it on some crappy grass courts… but it’s so weird to serve without not bouncing the ball.” – Brady [41:32]

• Online vs. in-store shopping (clothing):

  • Brady prefers shopping in person and almost never shops online;

    “I’ve online shopped once. I bought one pair of jeans. Ever.” – Brady [43:32]

  • Krawczyk and Keys: Love online shopping, especially to try at home and return.
  • Keys: “A lot of clothes don’t fit me correctly, so I have to buy multiple sizes of the same thing… Or I have to get, like, the tall sizes, which they never have in store.” [45:13]
  • Pegula: Hates it when store staff hovers; must vibe with them or leaves.
  • “I get so hot in those fitting rooms! Those lights are bright.” – Krawczyk [46:47]

• Nightmare shopping items & favorite brands:

  • Trying on jeans for tall/athletic bodies.
  • Pegula: “My entire closet is Free People and Adidas clothes.” [50:10]
  • Keys: Favorite Daughter, Abercrombie.
  • Krawczyk: Kukai, Abercrombie, Aritzia.
  • Brady: “Well, since I’m such a shopaholic… Abercrombie, Babolat…” [51:12]

Notable Quotes & Moments

• “You cave, lose your mind.” – Madison Keys on being upset when losing to someone you should beat [10:10]
• “No, I’ll hold it. Come sit down so that we’re both under the umbrella and not just getting poured on.” – Madison Keys [19:28]
• “There have been a few cuckoo coaches… some incidents where it’s like, I don’t think we’re coming back from this one.” – Madison Keys [22:47]
• “Coaches poaching players… I think that’s like, really shady.” – Jennifer Brady [25:33]
• “He lasted two weeks because of a trust thing…13 drinks that were charged to my room.” – Desirae Krawczyk [27:52]
• “I get major shoppies and I love an online shop. Love it. You just Apple Pay away.” – Madison Keys [43:55]

Funniest & Most Memorable Exchanges

• The group riffing on who wins “unforced error of the week”—especially bathroom/airplane and dog disaster stories [01:46–03:45]
• Sassy stories about on-court gamesmanship, fake medical timeouts, and psyching each other out mid-match [11:10–12:42]
• Banter about shanking balls into the stands and ball kid mishaps [13:01–15:09]
• Pegula’s deep-dive skepticism over Andy Murray coaching Novak, and the group’s Marat Safin fan-girling [31:15–35:58]
• Brady’s revelation that she’s only ever online shopped once in her life, to everyone’s stunned disbelief [43:17–44:10]
• Complaints about bad fitting room lighting and the trauma of trying on jeans as a tall athlete [46:37–49:59]

Timestamps for Major Segments

• 00:27 – Unforced Error / Winner of the Week
• 05:00 – Bachelorette plans & technical difficulties
• 06:25 – What Would You Do? (Tennis Hypotheticals)
• 19:59 – Coaching changes, hiring/firing, and gossip
• 36:30 – Fan Q&A (Dampeners, flex league advice, shopping quirks)
• 50:00 – Favorite clothing brands, shopping banter

Tone and Style:
True to the hosts’ witty, breezy, self-deprecating, and candid style—with spontaneous tangents, lots of friendly ribbing, and real insights into both the glamorous and less-glamorous aspects of pro tennis.

For Listeners Who Missed the Episode:
This episode is equal parts hilarious personal failures, honest shop talk, and lived-in tennis wisdom. The hosts pull no punches about the quirks and politics of tour life—and show that even the pros have their awkward, chaotic, or just gross moments. You’ll leave feeling like you’re in the locker room with four smart, funny friends.